Triazine based photoactive compound containing oxime ester

Abstract

The present invention relates to a triazine based photoactive compound containing an oxime ester group. The compound according to the present invention is a photoactive compound containing both an oxime ester group and a triazine group in one molecule, has excellent radical-generating efficiency due to effective absorption of UV radiation, particularly i-line (365 nm) radiation and can function as an effective initiator for photopolymerization of various compounds containing unsaturated groups, particularly an acryl compound.

1. A triazine oxime ester based photoactive compound of formula (1): 
       
         
           
           
               
               
           
         
         wherein n is an integer of 1 or 2; 
         when n=1, R is selected from the group consisting of a C 1  to C 6  alkyl group, a C 1  to C 6  haloalkyl group, a C 1  to C 6  alkyl group substituted with one or more groups selected from the group consisting of NL 2 , OL and SL wherein L is a hydrogen atom or C 1  to C 6  alkyl group, a phenyl group unsubstituted or substituted with one or more groups selected from the group consisting of a C 1  to C 6  alkyl group, a halogen atom, a nitrile group, OH and COOH, and a C 2  to C 5  alkylcarboxyl group; 
         when n=2, R is selected from the group consisting of a C 2  to C 6  alkylene group, a 1,2-phenylene group, a 1,3-phenylene group, 1,4-phenylene group, 
       
       
         
           
           
               
               
           
         
         R′ is selected from the group consisting of a hydrogen atom, a C 1  to C 6  alkyl group, a nitrile group and a phenyl group; 
         X is a C 5  to C 20  arylene group unsubstituted or substituted with one or more groups selected from the group consisting of a halogen atom, CN, a C 1  to C 6  alkyl group, a C 1  to C 6  alkoxy group, a C 1  to C 6  alkylthio group and a morpholino group; a divalent C 4  to C 20  heterocyclic group containing O, N or S, unsubstituted or substituted with one or more groups selected from the group consisting of a halogen atom, CN, a C 1  to C 6  alkyl group, a C 1  to C 6  alkoxy group, a C 1  to C 6  alkylthio group and a morpholino group; or a compound of the following formula (2): 
       
       
         
           
           
               
               
           
         
         wherein Z and Z′ are each independently selected from the group consisting of CH 2 , O, S, NR″ wherein R″ is a hydrogen atom or C 1  to C 6  alkyl group, and CH═CH; 
         l and m are an integer of 0 to 2, provided that l+m is not 0; 
         A is a simple linkage, or one selected from the group consisting of C p H 2p , O(CH 2 O) p , CH═CH, NR′″, S, O, S═O, SO 2 , and C═O wherein p is an integer of 1 to 6 and R′″ is a hydrogen atom or C 1  to C 6  alkyl group, provided that A is not a simple linkage when l+m=1; and 
         Y and Y′ are each optionally selected from the group consisting of a hydrogen atom, a halogen atom, CN, a C 1  to C 6  alkyl group, a C 1  to C 6  alkoxy group, a C 1  to C 6  alkylthio group and a morpholino group. 
       
     
     
       2. The triazine oxime ester based photoactive compound according to  claim 1 , wherein in the formula (1), when n=1, R is a methyl group or a phenyl group;
 when n=2, R is an ethylene group or a tetrahydrophthalene group; 
 R′ is a hydrogen atom, a methyl group or a phenyl group; and 
 X is selected from the group consisting of a phenylene group, a biphenylene group, a styrylene group and the following structural formulae: 
 
       
         
           
           
               
               
           
         
         wherein B is one selected from the group consisting of CH 2 , O, S, NR″ wherein R″ is a hydrogen atom or C 1  to C 6  alkyl group, and CH═CH; and 
         Y and Y′ are each optionally selected from the group consisting of a hydrogen atom, a halogen atom, CN, a C 1  to C 6  alkyl group, a C 1  to C 6  alkoxy group, a C 1  to C 6  alkylthio group and a morpholino group.